Bromination and dehydrobromination of exocyclic olefin 8 resulted in the formation of bromomethylene compound 9 and Wagner-Meerwein rearrangement product 10. The dehydrobromination of 10 with potassium tert-butoxide provided the corresponding bromomethyl compound 11 in high yield. Reaction of 11 with Zn-Cu couple in methanol afforded the methyl derivative 12 and the parent olefin 8. The unusual formation mechanism of 8 has been discussed in term of a reductive retro-Wagner-Meerwein rearrangement.